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139459

Sigma-Aldrich

Methyl crotonate

98%

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About This Item

Linear Formula:
CH3CH=CHCOOCH3
CAS Number:
623-43-8
Molecular Weight:
100.12
Beilstein/REAXYS Number:
1720292
EC Number:
210-793-7
MDL number:
MFCD00009287
UNSPSC Code:
12352100
PubChem Substance ID:
24848413
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.423 (lit.)

bp

118-120 °C (lit.)

density

0.944 g/mL at 25 °C (lit.)

SMILES string

COC(=O)\C=C\C

InChI

1S/C5H8O2/c1-3-4-5(6)7-2/h3-4H,1-2H3/b4-3+

InChI key

MCVVUJPXSBQTRZ-ONEGZZNKSA-N

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General description

Methyl crotonate undergoes vinylogous aldol reaction with enolizable aldehydes in the presence of aluminum tris(2,6-di-2-naphthylphenoxide).

Application

Methyl crotonate was used to investigate chemoselectivity in the reaction between methyl crotonate and benzylamine catalyzed by lipase B from Candida antarctica using solvent engineering. It was used as starting reagent during the total synthesis of phytotoxins solanapyrones D(1) and E(2).

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

30.2 °F - closed cup

flash_point_c

-1 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hisahiro Hagiwara et al.
The Journal of organic chemistry, 67(17), 5969-5976 (2002-08-17)
The phytotoxins solanapyrones D (1) and E (2) have been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate. The decalone was transformed into a solanapyrone core by
Jeffrey A Gazaille et al.
Organic letters, 14(11), 2678-2681 (2012-05-25)
The synthesis of the novel Lewis acid, aluminum tris(2,6-di-2-naphthylphenoxide) (ATNP), and its use in the vinylogous aldol reaction between methyl crotonate and enolizable aldehydes are described. ATNP is related to Yamamoto's Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH), but the 2-naphthyl groups
Solvent engineering: an effective tool to direct chemoselectivity in a lipase-catalyzed Michael addition.
Priego J, et al.
Tetrahedron, 65(2), 536-539 (2009)

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